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Rick Santorum has not run as a friend of labor unions, going so far as to reverse himself and embrace a national right-to-work law, yet the social conservative got a major boost Monday in Ohio from the big-money intervention of an unlikely source: one of the country’s premier unions.

The real endorsement of the American Federation of State, County and Municipal Employees (AFSCME) will go to President Obama. But with a half-million-dollar ad purchase aimed at persuading voters in the Ohio Republican primary not to vote for Mitt Romney, disclosed Tuesday, the union seems to be working hard for a Santorum-versus-Obama faceoff in November.

The unusual meddling by the Democratic money machine in a Republican primary is just a part of a wild set of strange bedfellows that has emerged in upcoming primary states. As the liberal group reaches out to conservatives to encourage them not to vote for Mr. Romney in Ohio, Mr. Santorum’s campaign actively solicited votes from another unlikely demographic: registered Democrats in Michigan.

Meanwhile, a previously sleeping super PAC designed to ensure the re-election of Mr. Obama, Priorities USA Action, has chosen Michigan to begin to stir to life, running its first major ads designed to inflict on Mr. Romney the embarrassment of losing his onetime home state.

Together, the curious allies have found, they have been able to pass a remarkable milestone: In a race previously defined by an overwhelming barrage of ads financed by a few wealthy Romney business associates, anti-Romney groups in Ohio have outspent the pro-Romney super PAC Restore Our Future, federal money-in-politics disclosures show.

The moves indicate that Democrats sense they are the ultimate victors in a drawn-out and increasingly negative campaign for the Republican nomination, in which a decisive front-runner has been slow to emerge. But the fleeting alliances also have shown that Mr. Santorum is far from ready to cede that title.

On Monday, the campaign of Mr. Santorum, a former senator from Pennsylvania, called Democrats in Michigan encouraging them to cast strategic votes for Mr. Santorum to derail Mr. Romney’s path to the nomination.

Meanwhile, an unaffiliated conservative political action committee spent tens of thousands of dollars calling Republican supporters of Rep. Ron Paul of Texas and former House Speaker Newt Gingrich, pleading: “No matter who your preferred candidate might be down the road, if you want to stop Mitt Romney, Rick Santorum needs to stop Romney in Michigan.”

It is the second time AFSCME has intervened in the elections of a party it opposes, pioneering the tactic in Florida last month with a $1 million buy attacking Mr. Romney.

On Monday, it spent a half-million dollars on television, radio and Internet ads in Ohio, federal disclosures showed. Its ads hammer Mr. Romney for opposition to the bailout of automobile companies, in which it says, “an entire industry was saved, 1.4 million jobs preserved.”

“Let them go bankrupt,” Mr. Romney says in the ads. “Romney would have turned his back on us in the depths of the recession, but he supported giving the banks billions in bailouts? That’s Mitt’s world. Why would we want to live in it?”

Mr. Santorum has staked much on Ohio, with a super PAC supporting him spending nearly $800,000 there compared with $1.1 million by Restore Our Future — a much closer matchup than in other states, where Mr. Romney’s far larger PAC has dramatically outspent Mr. Santorum‘s.

The positioning of Mr. Santorum as a candidate who could be propelled to victory by collecting “not-Romney” sentiment is made possible in part by the absence of Mr. Gingrich in the ad wars. A super PAC supporting Mr. Gingrich, also better-funded than the Santorum one, has spent only $70,000 in Ohio and been absent in Michigan.

In Michigan, the Romney super PAC has spent $2.3 million compared with $900,000 by the Santorum PAC.

The carnage in Michigan was made possible largely by state laws governing its primary Tuesday that allow registered voters to choose which party’s primary they want to participate in when they get to the polls.

Priorities USA Action, the Obama super PAC, also spent $230,000 attacking Mr. Romney in Michigan, making it the first state in which the PAC has become significantly involved. The group, which has struggled to raise funds, has spent only $800,000 overall. In all cases, the Democratic group has fought for Mr. Obama’s election by encouraging Republicans not to vote for Mr. Romney.

It was unclear whether the super PAC hoped to garner anti-Romney votes from Democrats or whether it hoped only to push Republicans to the right.

AFSCME is the only union to get involved in the election so far with the exception of $145,000 in anti-Romney radio ads from the Service Employees International Union in Florida and Nevada, but unions will be major players in funding ads as the general election nears.